Free Agency begins in earnest this weekend in MLB and one of the most interesting potential Free Agents is OF Josh Hamilton. He’s had really strong seasons in four of six seasons in the big leagues and is coming off an uneven, but ultimately above average 2012.

And then there are the Hamilton qualifiers. He’s entering Free Agency in his age 32 season (much later than a premier guy ever should) and he has a history of substance abuse and injuries. He has an MVP award and many playoff appearances, but when you throw this whole thing into a blender it turns out a product we’ve never seen before.

Josh Hamilton is the least typical FA we’ve ever seen. Former #1 pick, amazing tools, several good seasons. Old, injury prone, troubled past, terrible plate discipline, terrible middle part of 2012. What do you make of this if you’re an MLB club? What is the market for Hamilton and what should he reasonably ask for? Who takes the plunge?

To start off, Hamilton’s career WAR numbers look like this.

2007: 2.6 (337 PA)

2008: 4.1

2009: 1.4 (365 PA)

2010: 8.4

2011: 4.1

2012: 4.4

So if we’re willing to say that 2009 was the outlier and 2010 is the peak, Hamilton looks like a pretty stead 3.5-5.0 WAR player. That’s a tremendously valuable guy. Not quite perennially MVP, but he should make All-Star teams and hit in the middle of your order. But those numbers obscure underlining problems.

Obviously the substance abuse itself is worrisome, all other things being equal, but what would concern me most is that Hamilton did damage to his body in his early 20s that is going to catch up with him more and more as he ages. By traditional standards, Hamilton is already over his peak age as a baseball player and my guess would be his years of abuse will make that aging curve more problematic.

Additionally, Hamilton has put up some monster numbers, but has a really bad approach at the plate. No one is baseball swung at more pitches outside the strike zone in 2012. Actually, no one swung more period than Hamilton. In a lot of plate appearances I watched this season, Hamilton looked disinterested and swung at everything. If the ball made it to the plate, Hamilton was hacking. It cost his team in the middle and late part of the season as teams learned not to throw him strikes. This showed up in a big way because the Rangers lost the division by one game, so any marginal win would have been worth a lot to the team. If Hamilton could have improved his approach enough to win one more game, the Rangers would have made the playoffs instead of losing in the play in game.

So let’s talk contract details if we only look at what Hamilton has going for him. I’d wager to say an all good news Josh Hamilton is looking at a 7 year, $150 million deal. That pays him about $21 million per season which is right on par with what teams tend to pay per WAR. However, this is a good year to be a Free Agent and a lot of teams would pay handsomely to someone with Hamilton’s tools because the next best option might be BJ Upton. Let’s inflate Hamilton’s deal to 7 years, $170 million.

Now let’s evaluate Hamilton with only what he has wrong with him. He’s 32 and had some really big red flags pop up on the field this year, not to mention the potential aging problems we discussed earlier. You’re aware of his skill, but the other stuff is big. I’d say 3 years, $45 million. You want a shorter deal and fewer dollars, but you recognize he could give you 3 4.0 WAR seasons and are willing to gamble.

So how do those visions come together? Obviously the soft market is a big plus for Hamilton’s value. He doesn’t have Matt Holliday and Ryan Braun to compete with, so the dollars go up. When he’s on, the reward can be very high. MVP high. That pushes the dollars up. But he’s old, even if you are willing to offer a high yearly value, you don’t want to commit that much to a 38 year old Hamilton. Was the terrible July 2012 an outlier or a preview?

My sense is that someone with enough cash and enough guts will push north. 5 years, $100 million seems reasonable. But I’d set the range at 3 years, $50 million to 7 years, $170 million. That’s a wide space to drive a contract through. I can’t remember another Free Agent who could command such a strange distribution of offers.

If I’m a GM, I pass on Hamilton unless the price is in the bottom of the distribution. I only want Hamilton if everyone else undervalues him. I would not pay Josh Hamilton what he should earn. I would only pay him less, because he’s asking me to trust him that he can maintain his level of play for a long term deal.

If Hamilton and his agent walk in and ask for 7 years, my answer is no unless it’s for $80 million or less. 6 years I’ll go for $100 million. 5 years $90 million. 4 years I’ll go $75-80 million. If you picture this, I’m basically saying the more years he wants the less I’ll offer in AAV. I can’t risk $25 million to 2018 Hamilton. I just can’t.

So where does this leave us? Who makes sense for Hamilton?

MLB Trade Rumors postulated that the Rangers will end up winning the bidding after other teams show Hamilton that they won’t pay the big dollars. I think there are a couple teams who intrigue me as possible suitors (with percentages).

White Sox (25%)

Rangers (22%)

Other (11%)

Brewers (10%)

Mariners (10%)

Orioles (5%)

Red Sox (5%)

Yankees (5%)

Phillies (5%)

Blue Jays (2%)

Mainly this is all pretty much the prevailing opinion except for the White Sox. I think they make a ton of sense. There’s room in the OF. Konerko and Dunn are both in the last two years of their deals with Konerko closing in on retirement. Konerko is a FA after 2013, Dunn after 2014. Rios after 2014. Alexei Rameriz is the only position player signed into 2015 with any sort of dollar value (and John Danks is the only pitcher).

Viciedo is a very tradable player if you want to go Hamilton, De Aza, Rios across the outfield, or you could go Viciedo, Hamilton, Rios and find buyers for De Aza. He’s not blocked in 2013 in the OF. If you look to 2014, if Konerko retires, Hamilton can play the OF if he’s able or move to DH with Dunn going to 1B. If Hamilton can wait until 2015 to break down, the DH spot is wide open.

The payroll is there. The spot is there. The need is there. The White Sox are a team in the 80-85 win zone where one big player could make a difference and they might just be crazy enough and gutsy enough to go for it.

I think it’s more likely Hamilton signs in Not Chicago than in Chicago, but if you told me to pick one team, that’s the team to watch. Hamilton is a unique Free Agent, so it’s anyone’s guess.